Meet Jen! A member of fashion royalty…

American Classic – Day 26


Jen, my oldest friend, has kindly agreed to take the Proust Fashion Questionnaire for me today.  Jen and I grew up next door to each other and some of the best memories of my childhood are my times with Jen.  She’s super smart and wickedly funny and has a leg that should be in the Kickball Hall of Fame.  Normally, I like to pick someone who is struggling with fashion like I am, but since this month is American Classic, I felt perfection was necessary, and that’s where Jen comes in…


Jen happens to come from the most well-dressed family I have ever known. They lived their lives as if inside a Ralph Lauren catalog, playing miniature golf with sweaters tied around their necks.  Some days it was hard to tell where the preppy curtains ended and the family began.  It was like they were constantly dressed for a “what happens if we all have to go to the country club” fire drill.  Needless to say, when I went to Jen’s house to play I felt like a child from a Charles Dickens novel, wearing fingerless gloves and begging for a bowl of soup.

That high fashion esthetic remains today — Here is Jen and her entire family on a recent cruise…


My family didn’t even get this dressed up for my wedding

Over the years, Jen has slightly broken ranks with the family’s strict American Classic fashion code and ventured more into Euro chic, but still, her high standards remain, and like most royal fashion families, she has passed those standards onto her 8 year old daughter, Lauren.  I could be in a ball gown and Jen in pajamas and somehow she would look more “put together.”  I have learned over the years (and with a lot of therapy) that there is simply no competing with some families.  With some families, it’s best to just stand back and applaud.

“The Proust Fashion Questionnaire”  Jen…


What is your greatest fashion fear?  Having some kind of wardrobe malfunction. Just the other day my shirt became unbuttoned when I tucked my sunglasses into it and I inadvertently flashed my daughter’s friends at lunch.

Which historical fashion figure do you most identify with?  I would have to go with Coco Chanel. She got rid of the corset and made clothes simple, elegant and comfortable. 

What are you wearing in perfect fashion happiness?  Jeans and a black shirt and a really expensive pairs of shoes.

What physical trait do you most deplore in yourself?  Spider veins. Spider veins. Spider veins. Oh, and age spots on my arms (it’s payback for calling my mom salami arms as a kid).

On what occasion do you lie about your appearance?  Every chance I get.

What is your greatest fashion regret?  I once wore a pair of my mom’s white pumps to high school. Kristin Dickinson still references this fact today!

What outfit were you the most happiest in?  My white Izod shorts and yellow Izod shirt as a kid.

What is your most treasured fashion possession?  A black silk turtleneck that I have had since college. 

If you could change one thing about yourself, what would it be?  I guess I wish I could be more forgiving. Don’t ever cross me!


What is your most marked physical characteristic?  My smile.

What type of clothing do you most like to see on a man?  I don’t like to see no clothes on a man. Ok. Kidding. I like a man in a nice suit. 

What type of clothing do you most like to see on a woman?  Clothes that aren’t too tight and that aren’t too revealing. We all know what’s underneath.

Who are your fashion heroes in real life?  Katherine Hepburn. Lauren Bacall. Jackie. They made it look so simple. Ok. They are dead. But they dressed right! I am not sure anyone is doing this today.


What fashion trend have you most disliked?  Ballet flats. No one. I repeat no one, looks good in them.

What is your fashion motto?  Black goes with everything.


  • Tao of Tina says:

    I SO agree with the ballet flat shoe thing. Totally.

  • Kris Costello says:

    Am lovin’ your blog. I so relate to much of what you’re saying and love seeing the different styles (from one who hasn’t yet mastered any style). Anywhoo…a question: I’m having trouble discerning between American classic and euro chic. Can you please point out the differences? Thanks so much!

    • My Year of Fabulous says:

      Thanks! You know, I was thinking the same thing about euro chic and American classic. Very subtle differences… I will investigate.

  • Daniela says:

    Ha ha – I share your thought on the ballet flats! Not even do they look terrible, but the only way of movement in them is to waddle!

    Greetings from Germany


  • Bo says:

    She even knows how to answer questions with style! Really beautiful family-Jen’s mom looks so great! Perfect write up Holly!

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